2-Pyridineethanamine → HCID 67776389, compound

HRID 2405480Notes

Reaction equation

HRID 2405480 reaction equation
Cl[C:2]([C@:4]12[CH2:39][CH2:38][C@@H:37]([CH:40]([CH3:42])[CH3:41])[C@@H:5]1[C@@H:6]1[C@@:19]([CH3:22])([CH2:20][CH2:21]2)[C@@:18]2([CH3:23])[C@@H:9]([C@:10]3([CH3:36])[C@@H:15]([CH2:16][CH2:17]2)[C:14]([CH3:25])([CH3:24])[C@@H:13]([C:26]2[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=2)[CH2:12][CH2:11]3)[CH2:8][CH2:7]1)=[O:3].[NH2:43][CH2:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=1>ClCCCl.CN(C1C=CN=CC=1)C.O>[CH:40]([C@H:37]1[C@@H:5]2[C@@H:6]3[C@@:19]([CH3:22])([CH2:20][CH2:21][C@@:4]2([C:2](=[O:3])[NH:43][CH2:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][N:47]=2)[CH2:39][CH2:38]1)[C@@:18]1([CH3:23])[C@@H:9]([C@:10]2([CH3:36])[C@@H:15]([CH2:16][CH2:17]1)[C:14]([CH3:25])([CH3:24])[C@@H:13]([C:26]1[CH:35]=[CH:34][C:29]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:27]=1)[CH2:12][CH2:11]2)[CH2:8][CH2:7]3)([CH3:42])[CH3:41]

Participants

6

Reactant 2

HCID 759192-PyridineethanamineHCID 86666173HCID 86666173, compound

Product 1

HCID 67776389HCID 67776389, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

To a flask containing methyl 4-((1S,3aS,5aR,5bR,7aS,9S,11aS,11bR,13aR,13bR)-3a-(chlorocarbonyl)-1-isopropyl-5a,5b,8,8,11a-pentamethylicosahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate (77 mg, 0.13 mmol) in DCE (2 mL) was added Hunig'sBase (0.068 mL, 0.390 mmol), DMAP (1 mg, 8.19 μmol), and 2-(2-Aminoethyl)pyridine (0.031 mL, 0.260 mmol). The mixture was stirred for 2.5 hours at rt. The reaction was diluted with 5 mL of water and was extracted with dichloromethane (3×5 mL). The combined organic layers were dried with Na2SO4. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by Biotage flash chromatography using a 0-75% ethyl acetate in hexanes gradient. The fractions containing the expected product were combined and concentrated. The expected product, methyl 4-((1S,3aS,5aR,5bR,7aS,9S,11aS,11bR,13aR,13bR)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-3a-(2-(pyridin-2-yl)ethylcarbamoyl)icosahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate (0.062 g, 0.091 mmol, 70.0% yield), was isolated as a white foam. LCMS: m/e 679.7 (M−H)−, 3.09 min (method 3).

Workup

  1. extractionwas extracted with dichloromethane (3×5 mL)
  2. dry with materialThe combined organic layers were dried with Na2SO4
  3. customThe drying agent was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by Biotage flash chromatography
  6. additionThe fractions containing the expected product
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b9b1a0af55e24516806c7db688b706ed
Source dataset
uspto-grants-2014_08
Patent number
US08802661B2

Reaction notes

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